


Sugar Daddy?

by EloquentSavage



Category: Teen Wolf (TV)
Genre: Alternate Universe - Human, Artist Stiles Stilinski, BAMF Lydia Martin, Bottom Derek Hale, Bottom Derek Hale/Top Stiles Stilinski, Human Derek Hale, Lawyer Derek Hale, Lydia Martin & Stiles Stilinski Friendship, M/M, Mentioned Laura Hale, Mentioned Sheriff Stilinski, Not Beta Read, Personal Ads, Prompt Fic, Prompt Fill, Stiles Stilinski Has a Big Dick, Stilinski Family Feels, Sugar Daddy, Top Stiles Stilinski
Language: English
Status: Completed
Published: 2015-01-20
Updated: 2015-01-20
Packaged: 2018-03-08 09:07:06
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 8,259
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3203654
Author URL: https://archiveofourown.org/users/EloquentSavage/pseuds/EloquentSavage
Summary: <blockquote class="userstuff">
              <p>Busy, attractive, professional male seeks male artist, musician, or college student for mutually beneficial live-in arrangement. Compensation fair and generous. Must be intelligent, enlightened, quiet, and useful. </p><p>Stiles meets the ad's requirements, easily, but is he crazy enough to answer it? Is Derek crazy enough to follow through? </p><p>You can find me on Twitter at StilessPillow if you're interested! <br/>or</p><p>Prompt fill porn with just a little plot. Cute, funny ending, a tiny bit of angst.</p>
            </blockquote>





	1. Not All Solicitation Ads Are Created Equal

_Busy, attractive, professional male seeks male artist, musician, or college student for mutually beneficial live-in arrangement. Compensation fair and generous. Must be intelligent, enlightened, quiet, and useful._

"It's such a hard call," Lydia sighed. "If you were a woman I would say no in a second, but male oriented guys make up less than four percent of the population, which in itself is a good reason to write a personal ad. Not to mention you draw so much, you never leave your house. The deck is stacked so high against you, statistically speaking, I'm obligated to say you should check it out on principle alone." 

Stunned by Lydia's answer, Stiles gaped silently. She was supposed to be talking him out of it. He handed her the paper and pointed out the ad expecting her laugh at him, or at least talk sense into him, not turn it into a legitimate discussion. 

"You think it's legit?" Stiles asked.

"I think it's more likely to be legit than an ad posted by a heterosexual male, but you're not here to talk gender politics," Lydia shrugged. "You should still be careful, very careful. Besides, an attractive, busy professional is exactly the kind of person you need to have a relationship with, and this might the only way you’ll meet one."

Stiles opened his mouth to argue, but Lydia was right. He thought the same thing, then talked himself out of it just enough to need a second opinion. 

"It's a very good sign, like you said, he doesn't ask for physical characteristics like all the others," she continued. "But he lists attractiveness as one of his own attributes. I think it's an attempt to find someone he can pleasantly co-exist with, not grossly objectify. I think if you met him you could ask him why he posted the ad in the first place. That alone will tell you whether you should pursue anything," Lydia pointed out. 

"I'm not--I really didn't think you'd be talking me into it," Stiles admitted. Taking the local, monthly queer newspaper back from Lydia, Stiles read the ad again. "You won't tell anyone? In case it works out? I mean, I think this sounds like a roommates with benefits sort of situation, and I don't want Scott or Jackson to be weird around him." 

"No, and don't tell him you’ve told me either. Make sure he knows you have people who watch out for you, but keep this conversation to yourself. If he's lonely, rich and looking for something like this, he values discretion," Lydia agreed. "If you like him, just make sure it's really something you want to do. Don't jump in to a complicated situation because it looks easy and different than your life now." 

Lydia's caution proved she had been listening when he complained lately. He wasn't sure if he should be grateful she understood, or ashamed that his biggest problem was sheer and unadulterated boredom. 


	2. Long Suffering Is One Way To Describe It

Pacing in front of the San Francisco Bellagio's made him look like someone to avoid. Stiles resolved to go in finally. He agreed to meet with the guy. He sounded really cool and nice in his emails. Standing him up would be such a jerk thing to do. Grey sweater, short black beard was a promising description, and it was just lunch. Stiles had nothing to lose. He stared at the door, twisting his hands nervously. At the last moment, right before his fingers brushed the door frame, he backed away again and leaned against the newspaper dispenser nearby. 

This was a terrible idea. He was acting desperate and weird. Stiles happily owned weird, but not desperate. He didn’t know how to explain his nervousness without sounding like a dick. He wouldn't have even bought the newspaper if they hadn’t done an article on Danny and his giant brain. Stiles was just bored, but he didn't want to tell the guy that. He didn't want to be the asshat who acted like he was too good for it, but the truth was Stiles read the newspaper cover to cover because he hated a drawing he was working on and was momentarily willing to do just about anything to avoid it. He didn't even know if he really wanted to change his life. He didn't know what he wanted at all.

The words in the ad did strike him though. They stood out, and were oddly compelling when it was easy to make fun of the rest. He was just entertaining himself though, and wondering how self respecting people could post ads like that, but most of them didn't really respect other people. It showed in the way they worded the ads. Whoever mystery guys was, he knew how to sling words. The guy's emails were gorgeous too. Articulate but short, funny, easy to read. He read them all twenty times at least. Stiles sighed and shook his head, pinching the bridge of his nose in a very Sheriff-like fashion. Speaking of, his dad would kill him for going on an anonymous date alone, then be really sad and ask Stiles why he was there to begin with. He was comfortable living with his dad, which was a problem his dad would never understand. 

Either way, twenty two was too old to be living at home, but it wasn’t old enough to be making decisions like he was about to make with a perfect stranger. Stiles had a pretty good life, and he was poking at it with a stick because he was too stupid to let it be. It felt like he tried so many different things to kick start his motivation, but maybe he hadn’t tried enough. He hated the few weeks of college he forced himself to attend. Everyone said that wasn’t long enough to get past the initial hate everyone had, but Stiles didn’t see anyone around him doing anything more than trudging through. He was working on a steady freelance art career instead of college, with his father's blessing. His dad was impressed and happy with what he accomplished. Stiles was a fool for questioning how good he had it. 

The door to Bellagio’s creaked open and a tall, handsome man came out, with a woman close behind. Stiles looked back down at his hands, unconcerned with the strange looks the people going in and out had been giving him. He was off-putting and inconvenient maybe, but he wasn’t hurting anyone by having a mental breakdown outside the pizza place. When a pair of worn, black leather shoes stopped in front of him, he looked up and found the same handsome stranger. He was watching Stiles curiously as the woman who came out behind him walked down the sidewalk with a pizza box in her hands. They weren't together. 

“Stiles?” the man asked. 

“No,” Stiles said breathlessly, his chest aching in disbelief. 

“Oh, I’m sorry,” the man apologized. 

“No, wait--no, I am Stiles. I was just--um. Wow, you’re not--” Stiles stammered and tumbled his way through an apology that never actually got out all the way. 

Attractive? This was his idea of attractive? The guy was so hot it was painful to look at him. Fuck you very much, universe. 

Pinching his nose again, Stiles wished he could take back the last few minutes. He had shown up early. He didn't think the guy would be there already, but he had obviously been watching Stiles pace and be nervous the entire time. This was going badly. Very badly. 

“Um, I’m sorry for startling you and making you so nervous. You can go if you like, but I would love to buy you a slice and try to convince you I’m not worth being nervous over, at all,” the guy smiled. 

He said that in his email when Stiles admitted he was nervous to meet him. Stiles imagined that meant he was too old, or dry and boring. This guy had a goofy smile that could melt the fucking face off the sun with it’s brilliant charisma. He was broad shouldered, tall, and unfairly sexy in his grey grandpa-like cableknit sweater and artfully messy hair. Stiles was doomed from the beginning, he just didn't know it till right then. 

“I’m sorry. I am nervous and my brain just--” Stiles pantomimed it falling out of his head, which made the guy laugh a little. “What’s your name anyways? Not DH I hope.” 

“Derek, my name is Derek.” He smiled again as he held out his hand. Stiles shook it quickly, and too firmly from the surprised look on Derek’s face. “C’mon,” Derek insisted, pulling Stiles to his feet before letting go of his hand. “I promise the sourdough pizza is worth it even if I’m a huge mistake.” 

More nervous than he was before, but in a completely different way, Stiles zombie walked through ordering pizza and a beer. He was dazed by Derek's easy smile and perfect calm. He drank the tallboy the second the cute waitress put it on the table and gestured for another. He needed some chill. Actually, he needed a lot of chill. She nodded and grinned, like he was really funny. It wasn’t funny. Nothing about this was funny at all. 

“I’m not--I don't usually drink, ever,” Stiles clarified when he noticed Derek raise his eyebrows. “I’ll sip this one, but--you know--social lubrication, right?” Stiles grinned, already enjoying the warmth spreading through his chest. His stomach was empty and he really never drank. Maybe the tallboy was a bad idea too, but it was like throwing a pencil on a bonfire. Did it really matter at that point?

“Alright. I guess I’d rather have a smile than that deer in the headlights look you were giving me earlier.” Derek smiled and gestured to Stiles’ face, which made him think about how little he had done to it before he left his house. “I’m a corporate litigator. I’m bad at skirting around awkwardness and making small talk, which is probably why I haven’t gotten a date in so long.” Stiles scoffed, not believing a single word of it, and interrupting Derek rudely. “I just--” Derek stumbled over his words like Stiles had derailed him. “I like getting to the point. Negotiating is my strong suit, obviously.” Derek scowled for the briefest moment, but that was the last thing Stiles wanted.

“I’m sorry, I’ve never done anything like this, ever. Nothing is my strong suit, except the art thing, but that’s--” Stiles gestured dismissively. 

“Amazing, beautiful work,” Derek interrupted. 

“How do you know?” Stiles snapped, regretting his tone the moment the words came out of his mouth. He never really told Derek who he was and the email he used was private.

“I had my IT guy look you up,” Derek admitted. “Didn’t you look me up?” he asked. “Of course you didn’t, you didn’t even know my name.” Derek shook his head like he was surprised. “If you would have searched the last email address I corresponded from, you would have found me. Name, work, and solid proof I’m not a creep.” 

“I didn’t think of that.” 

Stiles cheeks turned warm with embarrassment. He was the younger, tech oriented artist. The least he could have done before driving an hour into San Francisco was make sure the guy wasn’t a serial killer. Derek smiled softly, but his eyes followed the waitress who was walking toward them. Losing Derek’s undivided attention felt like he was being docked points. He showed up a wreck, and he was too niave to protect himself apparently. That wasn't screaming useful by any means. 

“I’ve been really busy with character designs for a game, concept work. I haven’t slept enough, or done much of anything except draw for the last few days. I’m sure you know what that’s like though, getting stuck in paperwork up to here.” Stiles gestured to his eyes. 

“I do. Sometimes all I do is work. And eat, so I can stay awake, all day, for days on end.” Derek smiled at the waitress, oblivious to the fact that Stiles put a spit shine on the truth. That he was too busy distracting himself with art to think about Derek and their meeting, which was the point. Derek nodded and thanked her when she set two beers in front of them. Stiles didn’t even notice Derek had ordered one for himself. “I like that you understand that, a lot," Derek smiled. "Some people think working like that is some kind of sin.” 

“No way,” Stiles shook his head emphatically. “I live for my work. I’m not a college student because I’m doing things they can't teach me fast enough. The technology I'm using would be obsolete by the time I had a degree in hand to use it.” 

“That’s cool though. I respect that. People like you blaze the path, so to speak.” Derek said encouragingly. “I know from a recent case that game technology is growing so quickly no one can keep up with it. Indie creators are popping up left and right, destroying the way everything has worked in the past. I’d say I hope you’re alive when the dust settles, but I don't think it ever will.” 

“No, people really like to be distracted. They keep finding better ways,” Stiles smiled. “I do other things too, but you’re right, the game designing is the most challenging, and it pays the best, when it pays off.” 

“You’re taking a gamble on yourself though, as much as the designers,” Derek pointed out, like that was a good thing. No one else ever thought that was a good thing. 

“I’m not a gamble,” Stiles smiled. He sounded cocky, but Stiles was hoping Derek was the kind of person he seemed to be. When he smiled back, confirming Stiles’ suspicions, that was it. He was in love. Derek was the whole package. Gorgeous, smart, driven, forward thinking, and he was a real, genuine, work-a-holic. “I guess something that confident sounds kind of dumb coming out of my mouth after how weird I’ve been.” Stiles turned the beer can in a wobbly circle against the tabletop as he spoke. 

“Not at all. You ask me about work, I know exactly what I’m talking about. Ask me what I know about successfully dating, movies, Taylor Swift, or why everyone seems to be putting bacon on everything, and I am lost. Complete tool,” Derek laughed. 

“Who is Taylor Swift?” Stiles teased, earning another goofy grin from Derek. The waitress came back with their pizza, smiling at Stiles like she approved of how well things were going now. Kaitlin was the name embroidered on her apron. He smiled back, thankful he had a quiet, unobtrusive cheerleader. “So,” he started as Kaitlin walked away. “I can obviously relate to the reclusive, work addicted, hermit thing, but why post the ad?” Stiles needed to know why. Lydia insisted it was the first real question he asked. Derek’s answer would make or break the deal. 

“My sisters,” Derek sighed. “I work with them and--I used to have someone. It ended badly. I threw myself into work, and I liked it better. They’re not on board. They aren't rude about it, but it’s all they care about anymore. They’re fixated on setting me up with weirdos and god knows who just because they happen to be gay, and they happened to know the guys.” 

“Oh, I have a gay friend. His name is Bob, do you know him?” Stiles pitched the joke, smiling when it made Derek cringe. “Yeah, I’m over that shit too,” he agreed. 

“I don’t expect anything. I just want them to meet someone nice, and too busy to be available for every family function so they can drop it already. I want them to treat me like their brother again, not a project.” 

“You don't have to live with someone to accomplish that,” Stiles pointed out. 

“That’s the biggest motivation, but not the only one,” Derek shrugged. “I have a huge house I live in alone, a freezer full of instant food even though I like cooking, and absolutely no desire to play the game. It’s hard on morale, and I don't have a lot of that to spare,” he admitted. "I don't want to sound bitter or cynical because that's not really it, this shit is just rigorous and I'm over it already." 

“Yeah,” Stiles cringed. “Hook up apps, dating websites, and blind dates are like a gauntlet of crazy you walk away from swearing to god you’ll never do again.” 

“But then someone, or the lack of someone talks you into it,” Derek said, finishing Stiles thought. 

“Then the cycle of regret starts all over again,” Stiles chuckled. He laughed for the same reason Derek probably did. It he didn't it would mean admitting it made them miserable. 

“What about you. Like you said, you’ve never done this sort of thing, ever,” Derek reminded him. 

“I read the ads when I was bored. I saw yours and it seemed like it was written by someone who needed me,” Stiles answered too honestly. 

The beer, the easy conversation, the goofy smiles had all lulled him into a false sense of safety. Derek wasn’t smiling anymore. He looked uncomfortable, and that was the last thing Stiles wanted. 

“I didn’t think I wrote enough. No one else responded,” Derek said quietly. 

“It was the useful part. That’s asking way too much from a starving artist, or transient college kid,” Stiles assured him, hoping his new found bravery would drown out the anxiety that was pounding in his chest again. “I grew up with a single dad. Sheriff in a small town. Works way too much, sleeps too little. I learned to be useful young so I wasn't too much of a pain in his ass.” 

“That would do it,” Derek nodded. Then he smiled, his former discomfort forgotten. “I really just meant being able to clean up after yourself and maybe do a load of laundry or two."

“Well, I can do all that, make a mean lasagna, and fix your car. I’ll even sew a few buttons back on, but you’d probably have to negotiate a bonus,” Stiles said enticingly. 

“Right,” Derek laughed. “Actually, adding clauses without raising the negotiated payment is kind of my specialty.” 

“No way,” Stiles grinned. “Nothing that shady gets past me.” 

“It’s not shady, not when it’s mutually beneficial to both parties,” Derek argued. 

“Mutually beneficial,” Stiles repeated. “I knew you were a lawyer or something when you used those words.”

Derek nodded, a tight grin on his lips proved he didn’t like being so transparent. “We should eat,” he said as he picked up his pizza. Derek folded his first slice in half, the same way Stiles did, and held it sideways as he took a bite. 

“New York,” Stiles said, pointing to the way Derek ate his pizza. “My mom was from there.” 

“I went to school there. Mets or Yankees?” Derek asked. 

“Mets, unapologetically,” Stiles answered. 

“We suffer for love.” Everything Derek said was perfect. 

There were a few scenarios that Stiles would have accepted as sane reasons to post the ad, and follow through with it, but Derek’s were really good. Stiles easily understood wanting people to stop worrying about you. Lydia was the only one who didn’t openly fixate on his lack of social life, but she was eyeballs deep in theoretical mathematics every day. She was happy he was alive and willing to listen to her rant over skype about imaginary numbers and the idiots who wielded them. 

“What did you mean when you said you didn’t expect anything?” Stiles asked. 

“Like sex, or anything like that.” Derek shook his head, still just as interested in the pizza as the conversation. “What I happen to let my sisters think about the guy who lives with me is one thing, pretending we’ll automatically be compatible just because we’re both dick oriented is as far fetched as the gay friend Bob working out. I realized after I submitted the ad I should have explicitly said so, but it said what I wanted, not a list of what I didn’t want. All those guys sounded like dicks trolling for a piece of ass. I’m not that guy. I get it though. We’ve all hooked up with someone just because he was there and willing,” Derek shrugged. 

“I haven’t,” Stiles admitted. Derek’s eyes snapped up, like he was stunned by the admission. “I’m not like, opposed to it. I just haven’t done anything like that before. Maybe it was the small town, or the high standards of all the other guys in it, but I’ve never....” 

“You said before with the apps and--” 

“I’ve been out there, but I haven’t snagged any of the wares, if you know what I mean?” 

“Sort of,” Derek said tentatively. 

“I’ve had a few dates. Guys from the gaming industry mostly, and one really hot mathematician, but no one has ever stuck. And no one temporary ever turned me on,” Stiles shrugged. 

“Some days I wish I could say the same,” Derek said. He nodded like he understood and went back to his pizza. “Why are you here then?” he asked after he finished off his slice. 

“I live with my dad because being on the cutting edge doesn't pay consistently, as you can imagine. It’s cool, but I still feel like I’m the same person I was when I was sixteen and decided this was what I wanted to do. The years keep slipping by and I keep accomplishing things, but not as much as I want to. I need to see if the comfort of home is stifling my upward momentum,” Stiles explained. 

“It is. I have five brothers and sisters and all of us had the exact same problem. Our parents were great, amazing people, but being that comfortable doesn’t make it easier to take risks. It makes it easy to rationalize staying comfortable.” Derek’s easy answer resonated with him profoundly. 

“Would you be weirded out if I said ‘Amen’ right now?” Stiles grinned. 

“Yes, a lot,” Derek laughed. 

“So, not religious then?” 

“Does worshipping Neil Degrasse Tyson count?” 

“I think it does, actually,” Stiles nodded in approval. “Have you seen pictures of him shirtless?” 

“No,” Derek laughed, stuttering over a mouthful of pizza like he was shocked such a thing existed. 

“Hot, like fire,” Stiles promised. 

“Really?” Derek asked, wide eyed. “huh.” 


	3. Is Adulting Really A Word?

“Wait, so why did you refuse the allowance?” Lydia asked. 

“I’m not taking cash Lydia. Are you kidding me? We both know I stress clean and cook like a fiend when I’m avoiding projects I hate. I can justify not paying rent or anything. He won't need his housekeeper anymore and he pays her way more. I mean, the difference is what he offered me in allowance, so I know exactly how much he was paying that stubborn harpie, but I’m not a prostitute now. Jesus,” Stiles argued. 

“But you’re not even sleeping with him,” Lydia argued back. “Oh, you want to sleep with him. That’s good,” she smiled hopefully. “I’m sorry, I haven’t slept in a couple days. I want to be better at this but--” 

“No, I know. How are things going anyhow?” Stiles asked as he packed up the last box from his room. 

“I want sleep, and answers, but I also want to know you’re sure about this. Like, really sure?” Lydia asked. 

“I am. I like him. Worst comes to worst I move back in with my dad and start over. Lord knows Dad would be happy. He cried last night at dinner, saying how much he’s going to miss me being around. I almost changed my mind right then.” 

“What did you tell him?” 

“The truth, except how we met and pretty much anything specific about Derek’s life. I said I met him through the gamers. He’s a corporate lawyer, so, you know? Nothing unbelievable. Like you said, it’s discretion. Adulty things. White lies,” Stiles shrugged. 

“Adulty...” Lydia asked incredulously. “Anyone who uses that word is not adulting.” 

“Pot, meet kettle,” Stiles said, pointing at her face on the computer screen, then to himself. 

“I never made claims,” She argued. “I’m sitting here talking to you from my dorm room, which hasn’t been cleaned in a week, suffering from insomnia induced euphoria. I fail at adulting. I am fully aware of that.” 

“Geez Lyd’s. I love you, and I’m fine, really. I’m excited. Derek is exciting. I’ll be fine, I promise. Go get some sleep,” Stiles said as he hovered over the end call button. 

“I love you too. Please don't get Single White Female’d,” Lydia asked sadly. 

“Please Lydia,” Stiles begged dramatically. 

“Okay, okay. Just text me so I can read stuff as soon as I wake up, okay?” 

“I promise, goodnight.” 


	4. We Came Here For The Conversation, We Stayed For The Sex

A baby blue Jeep ambled down the long driveway toward the house. Derek paced as he watched it out the long picture window. He walked into this plan thinking Erica was insane for concocting it, but now it was all he could think about. Other people had responded, but they didn't count because they were questionable, and didn't pass the strict filters Erica had put in place. Stiles was the only face Derek got to look at, and he knew right away he wanted to meet him. He wished their meeting was better, different, more organic, but that was almost impossible for people like them. 

Negotiations almost fell apart over the stipend Derek offered. He shouldn’t have. He could tell Stiles wasn’t the kind of person to agree to something like that, but he wanted to be generous. He hoped Stiles would say yes just because of how smitten he was and how charming he found Derek. Stiles made a joke about Derek being transparent once, but it was painfully obvious how much Stiles liked him. Still, Stiles said no to his heavy handed offer. Derek felt like such a dick trying to impress him when he obviously already had. He called Erica later that night and she fixed it, he hoped. Derek’s stomach ached with anxiety as Stiles pulled into the garage. He sat down in his big chair and picked up the Wall Street Journal, hoping he didn’t look anxious. 

The sound of keys in the side door leading to the garage preempted Stiles by a few seconds. Derek took a deep breath and put on his game face, then relaxed because his game face was fucking terrifying. 

“Hey, I wasn’t sure if you were really here, with the car. Don't you usually work?” Stiles asked. He set his bag down on the other chair and stood, looming over the living room in a way Derek was sure was only judgemental in his head. 

“I do, but I told my sisters my secret boyfriend was moving in today and they shit themselves with happiness. I had to get the fuck out.” 

“That bad?” Stiles cringed. 

Derek hadn’t meant to sell the sour mood so well. He was over reacting. “It’s fine. I just wish they would get that excited over my real accomplishments,” Derek complained, meaning it. 

“Sisters man, wanting you to be happy and shit. Fucking awful,” Stiles mocked him. 

“You won't think it’s so funny when you meet them,” Derek warned. 

“I have a while to maintain the illusion still, right?” Stiles asked as he picked up his bag and headed to his bedroom. 

“Yeah, I bought us a couple weeks by telling them you’re really anxious from the move. You need time to settle before they descend. They thought it was cute I was so protective.” It infuriated Derek how cute they thought it was. They were both tiny menaces. 

Unsure how Stiles would react to the changes Derek made to his room last night, he held his breath, bracing himself for anger, frustration, denial, maybe acceptance. Hopefully. 

“Derek, what is all this stuff?” Stiles shouted down the hall. 

“I went shopping,” Derek shouted back, unwilling to face Stiles until the last possible moment. It was a lie. Erica went shopping, and Boyd set it all up, but Derek’s black card paid for it. 

“Derek that’s--I’ve never even seen that model of tablet before, and the whole--all the things on the desk. The desk--” Stiles marveled. Stuttering painfully as he came back down the hall. “Why did you do that?” he asked. Stiles was stunned, but not angry or offended. It was a good start. 

“You needed a workspace,” Derek answered. 

“I have my computer, and my tablet. I was--” 

“Comfortable with it?” Derek interrupted, reminding Stiles why he was here to begin with. Derek was internally elated Stiles wasn’t telling him he had to take it back. He made Stiles wary of their arrangement before and it tore Derek up. He wanted Stiles around more than anything. “It’s new, better, unfamiliar. That’s what you wanted out of this, right?” 

“You are--wow...” Stiles shook his head like he wasn’t sure what to say. “You’re either really good, or really bad at negotiating. That had to set you back like--” 

“Nothing. It’s nothing compared to your time and what you’re going to do with it,” Derek insisted. 

Speechless, Stiles just stared at Derek like it was a little painful and he would rather be doing anything else. “I want to kiss you right now,” he blurted out. 

The sudden, stricken expression that engulfed his face was becoming the all too familiar hallmark of an accidental moment of honesty. Stiles was terrible at filtering himself, but Derek really liked that about him. 

It took Derek a moment to realize he needed to respond with more than just a smile. “I would really like that,” he said quickly. 

Thankful his voice sounded solid enough, Derek gripped his newspaper too tight trying to hide how nervous and shaky his hands were. Stiles took it out of Derek’s hands and tossed it on the end table before climbing into Derek’s lap. He was too tall, and too big, but Derek wrapped his arms around Stiles’ chest and held him close anyways. Long, demanding fingers threaded through Derek's hair as Stiles’ lips met his. He kissed like Derek was hiding something and only his tongue could find it. His teeth dragged over Derek’s bottom lip, nipping dangerously as Derek chased his mouth, looking for more. 

Disliking the awkward position, Derek pulled Stiles up on his lap. Stiles used the opportunity to run his hands over Derek’s arms and chest, his fingers trailing over heavy muscle as he shifted to straddle Derek’s hips. The new position gave Derek easy access to his whole body. His hands ghosted over Stiles' clothing, trying to decide if he should ask to peel it off or go slow and savor how good Stiles felt pressed against him. Stiles grabbed his hands and put them just inside the hem of his shirt impatiently, then pulled him in for another kiss. 

Obliging Stiles' silent demands, Derek ran his hands up inside the shirt, sliding gently over his smooth, warm skin. His stomach rippled under Derek’s fingers as Stiles moved against him eagerly. When his hips rocked forward and dragged over Derek’s roughly, Stiles stopped, suddenly, raspy and breathless. He looked down at Derek like he was unsure of something. 

“You know I didn’t--” Derek started to reassure him they didn't have to go any further.

“Shut up, please,” Stiles interrupted him, pressing his lips roughly against Derek’s again. “Do you want me?” Stiles asked through biting kisses he trailed over Derek’s neck and jaw. 

“Yes,” Derek whispered, unsure why Stiles asked. Derek thought the evidence was irrefutable. The only thing he wanted right now was Stiles. 

“Same,” Stiles agreed. “Your room,” he demanded. 

Derek picked them both up, surprised Stiles wasn't harder to move, but he was helping awkwardly, a little. Stiles walked backwards, stumbling as he stripped Derek’s shirt off, then his own. Derek kept his hands close to Stiles’ chest, assuring he wouldn’t fall while fumbling to get them both naked. He stopped for just a second to tear away Derek’s belt, then left his pants in a puddle on the floor. Stiles waited until he was standing at the end of Derek’s bed to start unbuttoning his jeans though. 

“I probably should have said something before, but I honestly didn't think I would have the guts to attack you like this for weeks.” Stiles was setting Derek up for some kind of confession while Derek rifled through his bedside table to make sure he had everything they needed. He stopped and gave Stiles his undivided attention when Stiles fell silent. “I don't expect anything, really.” Stiles assured Derek, using Derek’s words. That made him even more nervous. Stiles fidgeted with the buttons again. “I’m perfectly happy just getting my hands on you. I can get myself off just fine." 

Stiles’ words confused him, but he was obviously nervous and scared about what he wanted to tell Derek. 

"What are you talking about?" Derek asked when Stiles didn’t blurt it out like he expected.. 

"Nothing bad," Stiles assured him quickly. "Well, maybe. It depends. Top or bottom?” Stiles asked.

He sifted through his memory, all the things Stiles had disclosed about himself, the deeply personal facts they had both shared, but Derek couldn't remember anything that flagged concern. He had nothing to lose by answering.

“Versatile,” Derek answered. “Bottom preferred,” he added. There was no point in hiding what he usually wanted. 

“Oh, that’s um--awesome,” Stiles smiled like he was pleasantly surprised. It was a better reaction the Derek usually got. “Well, maybe. Um, I'm sorta big,” Stiles hesitantly gestured to the bulge in his pants. 

"How big?" Derek sat up, suddenly overwhelmingly curious if it made Stiles so nervous. 

Silently, Stiles slid his hands down his hips, his fingers stuttering over his pale skin in a thrillingly slow way. He wasn't trying to be sexy, he was scared of being rejected. Derek wanted to stop him, assure Stiles he shouldn't be so worried, but his eyes were fixed on the sinking denim. Stiles shifted himself before his underwear pushed all the way down, pulling out an intimidatingly large dick. His thin thighs masked the monstrosity hanging between his legs too well. Derek hadn't spent a lot of time looking, he liked Stiles' face and hands too much to pay a lot of attention to anything else. But still, he had no idea. 

“I can't tell what that’s all about,” Stiles said, gesturing to Derek’s expression. 

“Pleasantly surprised,” Derek answered quickly. He was torn between satisfying the thrilling curiosity and wanting to make Stiles feel much more comfortable. There was only one way to accomplish both. “Come over here,” Derek demanded. He slid his own boxers off as Stiles shed the rest of his clothes in response to Derek's eagerness. 

Watching Stiles crawl over the bed toward him made his dick ache with anticipation. He was all long, hard muscles. Thick, ropy veins crisscrossed his arms, contrasting beautifully with his boyish features. Derek imagined how rough and unrelenting Stiles would be if Derek gave him permission. The images flashing through his mind motivated him to grab Stiles and push him back into the pillows. The heady groan Stiles let out when Derek immediately began exploring his skin with his mouth was incredibly satisfying, and encouraging. 

When Derek made his way all the way down he dragged his lips and teeth across the thin, sensitive skin of Stiles lower stomach. Stiles hissed but his hips bucked up, chasing Derek’s mouth as he backed off, proving he liked it. Stiles threaded his fingers through Derek’s hair and held tight, demanding some kind of obedience already. Stiles waited, watching him curiously as Derek inspected the new and potentially endless supply of entertainment in front of him. Stiles was uncut and swollen, red with wanting. Derek wrapped his hand around him, marveling at how his fingers just barely touched when he closed them. He stroked slowly, his mouth hovering close. 

“Is this why you didn't do the casual thing? Afraid of terrifying people?” Derek asked. 

“Too much weirdness mostly,” Stiles nodded, confirming Derek’s suspicions. “It’s either a novelty or a deal breaker. I've never gotten that look though.” 

“What, like I want to eat you alive?” Derek asked. 

“Yeah, and um. Go ahead if you’re into it,” Stiles offered. 

Done wasting time, Derek slid his lips down over Stiles’ dick, pushing back his foreskin as he lowered himself. Stiles moaned and let go of Derek’s hair, only to grip it again as Derek started sliding up and down. He had to be careful with Stiles when it came to this. He didn’t want to be added to the list of people who made Stiles feel awkward or objectified, for both their sakes, no matter how excited he was, or how good Stiles tasted. Derek explored slowly, watching Stiles reactions. It wasn't easy holding back, but he was glad he did when he saw Stiles' eyes fixed on his mouth, his lips parted, eyebrows drawn up tight like it pained him to watch. He was already overwhelmed by what Derek was doing, and it wasn’t nearly as much as he wanted to. 

“Oh, god. I’m going to come if you keep it up,” Stiles said breathlessly. 

“You’re good to go again, right?” Derek asked. 

“A few times, especially with you,” Stiles smiled, letting out a breath that sounded like relief. 

Derek laid into him again, fiercely this time, sucking and stroking Stiles until his hips thrust into Derek’s mouth and his thighs were trembling. His balls tightened against his body when he was close. Stiles moved his hand over Derek’s hair like he wanted to warn him, but Derek was purposefully making it too intense for him to think that clearly. He wanted to watch Stiles fall to pieces. The sounds he was making, the way his skin was flushed from his chest to his cheeks, how his other hand trailed over his stomach, pressing and dragging over his own skin, that was all Derek wanted from him. 

Swallowing down, Derek slowed his pace, but kept trying to suck Stiles dry. He softened a little, and the sounds Stiles made went from urgent and desperate to low and appreciative. Derek was surprised Stiles let him work through his climax and didn't ask Derek to stop because he was too over stimulated. Stiles hands ghosted over his hair and shoulders, his expression falling somewhere between reverence and longing. Derek kept lapping and sucking slowly, enjoying the blissed out, satisfied way Stiles touched and appreciated him. 

“That was a fucking religious experience. Tell me you liked doing that as much as it looked like you did?” Stiles asked hopefully. 

“Uh huh,” Derek assured him, unwilling to stop just yet. Not when Stiles was getting hard again already. 

“Fuck, that’s hot,” Stiles cursed quietly. 

“Do you want to fuck me?” Derek asked, letting Stiles go only because he was ready for more promising things. 

Stiles looked up at him through heavy, black eyelashes. His expression was a mix of awe and confusion. “I want to, a lot, but I need a minute. Unless you want to be on top?” Stiles offered, attempting to be polite and accommodating. 

“Yeah.” Derek liked the idea mostly because he didn't have to wait as long. “Your hands are beautiful,” Derek said as he brought Stiles’ fingers to his lips. He wanted nothing more than to stroke himself, but he wanted to last through it. He licked up and down, getting Stiles wet before he covered his fingers with lube then rolled a condom down over his dick carefully. “We’ll special order some for you, they’ll feel better,” Derek promised. 

“You can do that?” Stiles asked. 

“Easily,” Derek assured him as he guided Stiles hands where he wanted them. 

Stiles kissed him lazily as his fingers circled Derek’s hole, playing and pressing lightly until his finger slid inside without resistance. Stiles was careful, and knew what he was doing. His other hand roamed over Derek curiously, testing his skin and scratching lightly with his blunt fingernails until he had two fingers sliding and scissoring comfortably. 

“God, you're fucking devastating to watch. I don't know if I’m going to survive this,” Stiles admitted. “Just watching you ride my fingers is making my dick so hard again. I want to fuck you so bad.” 

“Then fuck me,” Derek insisted, rolling his hips into Stiles’ hand eagerly. 

“Not yet.” Stiles scowled quickly, his expression softening as his hand trailed over Derek’s thighs. “Careful. I want to be careful with you,” he said. Pressing hard, needful kisses into Derek’s neck and chest, Stiles slipped in another finger stroked steadily. “I want you to feel good. You’re so gorgeous like this,” Stiles whispered in his ear, sending a shudder of bliss down Derek’s spine. 

“It does feel good,” Derek promised. 

He relaxed, forcing himself to slow down and enjoy the preparation instead of fixating on the pleasure of Stiles’ fingers inside him. He rocked his hips in slow circles, telling himself the longer Stiles worked into him, the better his dick would feel later. 

“I want you to love riding my dick. I want to make you hard just thinking about it,” Stiles whispered more boldly. Derek gasped at the heated thrill that tightened his already aching dick. “You’re so hard for me right now. I know you aren't touching yourself so you won't get off.” Derek pressed down on his fingers, already wishing it was more. “I want you to remember this. I want to see that hungry look on your face when you think about my dick inside you,” Stiles continued the devastating tirade of words. Derek let out a small, weak sound, begging Stiles to give him more. “Are you ready now? You feel perfect.” 

“Yeah,” Derek agreed. His heart was skipping beats and his body was trembling in anticipation, worked into a frenzy by Stiles hands and words. 

“I want you to get it all in before you start riding me. Grind down good. I wanna feel it deep inside you,” Stiles insisted.

Positioning himself carefully as Stiles slowly pulled out his fingers. Derek concentrated on staying relaxed as he lowered himself down on the thick, blunt tip of Stiles’ dick. He worked down further, gasping at how good the thick fullness felt. Stiles made it easy with all the preparation. He pushed down slowly until he couldn’t go any further, wanting to stroke and squeeze himself so much. It was a lot, stretched out and filled more than he ever had been before, but the way Stiles pawed at his chest and hips eagerly reminded him to rock his hips, grinding against Stiles in slow, deliberate circles. 

“Fuck,” Stiles cursed. 

Closing his eyes as he pulled himself tight against Derek, Stiles begged him to slow down with the steady grip he had on Derek’s hips, but he didn’t relent. He kept moving, eliciting louder, more frantic sounds from Stiles when he started working up and down. Derek forgot about himself for a while as he moved over Stiles, letting his hands dictate the slow, deliberate pace of Derek’s hips. 

“Jesus, you feel so good,” Stiles said, his voice barely more than a whisper. “Let me fuck you. I want to watch you come.”

His eyes grazed over Derek hungrily as he went still and braced himself above Stiles. Thrusting up slow and hard, Stiles moved to his waist for a better grip. His long, brutal fingers dug into Derek’s more forgiving flesh. Determined and unrelenting, Stiles picked up the pace. He wanted to watch Derek get off, and Derek suspected Stiles would lay into him mercilessly if Derek gave him what he wanted. 

The hot, blissful slide of Stiles’ inside him kept him teetering on the edge. He reached down and squeezed himself, pinching a little to dissipate the euphoric tension that had built up. He wanted to stroke himself good, give Stiles and himself a little time to enjoy it. Giving himself a couple of long, slow strokes made Stiles thrust into him harder. A quiet moan escaped past Derek's lips even though he didn’t usually make much noise. 

“Yeah, let me know you like it babe,” Stiles begged as he thrust hard and fast. Derek gasped, letting himself moan eagerly as he finally stroked his dick with purpose. The blissful, overwhelming ache built up too fast. He was bucking against Stiles too soon, thick ropy, white come covering his chest as Derek climaxed. “Yeah, thats what I need. So fucking beautiful,” Stiles kept talking, his words making Derek’s skin hot and more excited than his still spasming dick. “Give me all of it, I want it all,” Stiles urged him. 

“Your fucking mouth,” Derek marveled. His head swimming with bliss as he stroked himself dry. Stiles smiled and slowed down. “Please don’t stop,” Derek asked. 

“You like to be fucked after you come? Does that feel good?” 

“Please,” Derek begged, squeezing his still hard dick. The sweet, honey-like ache the euphoria left behind was almost as good as the climax itself. 

“Please what Derek? You want me to keep fucking you?” Stiles asked, running a hand down Derek’s sweat covered chest. 

“Please don't stop,” he asked again. He let himself go, leaning heavily on Stiles shoulders trying to keep himself upright. “Please.” 

“Hold yourself up on the headboard,” Stiles commanded, wrapping his hands around Derek’s ass, his grip tight and demanding. He thrust up, pushing himself deep into Derek as he rode out the lingering bliss. Suddenly Stiles was bucking up against him, his hands trembling as he moaned through clenched teeth. “Fuck yeah Derek, so good,” Stiles said almost incoherently as he drove himself hard. 

The obscene wet, slapping sounds slowed as Stiles finished. His breath came hard and raspy as his hands grazed over Derek’s long, exposed chest. Derek held himself up over Stiles, but tipped his hips back and took him in deep again, grinding against him slow and hard until Stiles’ dick stopped spasming inside him. 

“Come here,” Stiles demanded, pulling at Derek’s arms. He settled against Stiles’ chest, letting himself relax a little as Stiles ran his hands over Derek’s neck and shoulders. “That was so good. No one has ever made me feel like that before. I’ve never seen anything as hot as you are when you come. I wanna make you feel that good all the time.” The waves of approval kept pouring out of Stiles like he knew what it did to Derek. He was loose boned and his skin felt alive and ecstatic. The fullness of Stiles still inside him felt good, stretching him out and nudging against his most sensitive parts. 

The shallow breaths Derek listened to along with Stiles’ slowing heartbeat forced Derek to notice how slack he had gone. “I’m sorry, I’m too heavy,” Derek apologized, bracing himself to get up.

“No, stay, please. You’re perfect. You can stay like this as long as you want,” Stiles assured him. His hands worked over Derek’s neck and back, pressing and rolling his muscles lightly, like Stiles wanted to make sure the tension drained out of him again. Derek moaned quietly, settling back against Stiles as he turned to putty under his strong hands. “Oh, god. Those sound you make. I could be hard enough to fuck you again just from hearing those sounds,” Stiles confessed. 

“I’m usually quiet, but you’re good,” Derek added to the confession. He slipped his hands under Stiles’ back as he buried his nose against the dense, thick patch of hair at the center of his chest. “You fuck like a gladiator.” 

“It’s all you. You make me rock hard. I’ve been talking my dick down the whole time we’ve been working this out. I wasn’t sure you wanted it, and you’re so hot. Jesus christ you’re hot.” Stiles voice was thick and raspy. “Can we do this again after dinner?” he asked. 

“Which part?” Derek asked. 

“All of it, but next time I wanna fuck you against the kitchen counter. Lean you over, my hands on your shoulders. You take it so good,” Stiles said as he pulled Derek up to his lips. Stiles kissed him hard and possessive, his tongue darting over Derek’s lips like he could still taste himself there. “Maybe I’ll stretch you out on the couch and fuck you from behind so I can stroke you off. I don’t know though. I like watching your face as you take it all.” 

“Oh, my god.” Derek breathed heavily against Stiles’ skin, thrilled by the graphic indecency of his words. 

“You want me to tell you how hot it is watching you take my dick?” 

“Yes, graphically, but in the shower?” Derek offered as he righted himself. Sitting back heavily made him smile as Stiles groaned. 

“Oh, my god!” a high pitched female voice shouted, startling both of them. Cora’s nervous, embarrassed laughter rang out through the house as she called out to Laura not to come inside. 

Derek sighed and covered his face with his hand as the front door closed loudly, announcing the house was empty again. Giving Cora a key was the worst idea he ever had. 

“Well, um... I guess we won't have to sell them on the boyfriend part anymore, will we?” Stiles laughed.

**Notes for the Chapter:**

> [ The legendary dick itself ](http://theysortalooklikeyou.tumblr.com/post/128256899064)


End file.
